The development of organometallic catalysts that exhibit good reactivity while concurrently offering chemoselectivity between similar functional groups are often at odds with one another. These challenges culminate when preparing biologically important molecules or modifying existing scaffolds to investigate structure activity relationships as these high-value substrates often contain functional groups with cross reactivity. The ability to develop catalysts capable of performing precise modifications remains a highly sought after goal in academic and industrial research. Demonstration of these protocols represents a major triumph in catalyst design and synthesis which leads to the next generation of biologically relevant compounds with life-saving properties. This proposal outlines a strategy that combines organometallic catalysis with supramolecular clusters to circumnavigate the inherent issues of cross reactivity and achieve chemoselective and ultimately enantioselective transformation on complex molecular scaffolds. Supramolecular clusters have a demonstrated ability to endow unique reactivity in organic and organometallic transformations through a dynamic microenvironment that benefits from numerous non-covalent interactions. Inspired by these successes, the research program outlined in this proposal offers two paths which build from promising initial results I have gathered. Ultimately, the investigation of enantioselective transformation will reveal the non-covalent interactions of a supramolecular cluster and organometallic catalysts, yielding a unique view of how dynamic microenvironments influence catalysis. The proposed research ultimately seeks to develop methods that will facilitate the preparation and modification of structurally complex medicinally relevant molecules in a novel way concomitantly expanding scientific knowledge.